Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior
Identifieur interne : 001159 ( PascalFrancis/Corpus ); précédent : 001158; suivant : 001160Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior
Auteurs : Pawel Gawrys ; Anna Zoltowska ; Malgorzata Zagorska ; Adam PronSource :
- Electrochimica acta [ 0013-4686 ] ; 2011.
Descripteurs français
- Pascal (Inist)
- Copolymère alterné, Polymère électroactif, Imide copolymère, Semiconducteur, Synthèse chimique, Spectroélectrochimie, Thiophène dérivé copolymère, Spectrométrie UV visible, Propriété électrochimique, Voltammétrie cyclique, Semiconducteur organique, Polymère conducteur, Naphtalène-1,4,5,8-tétracarboximide dérivé, Benzo[lmn][3,8]phénanthroline-1,3,6,8-tétraone dérivé.
English descriptors
- KwdEn :
Abstract
Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-terthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.
Notice en format standard (ISO 2709)
Pour connaître la documentation sur le format Inist Standard.
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Format Inist (serveur)
NO : | PASCAL 12-0325093 INIST |
---|---|
ET : | Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior |
AU : | GAWRYS (Pawel); ZOLTOWSKA (Anna); ZAGORSKA (Malgorzata); PRON (Adam); BERGEL (A.); BOND (A. M.); BRANKOVIC (S.); BULTEL (Y.); DI QUARTO (F.); GORTON (L.); INZELT (G.); LAPICQUE (F.); LISDAT (F.); OPALLO (M.); SAVINOVA (E. R.); TOH (C.S.); TSIRLINA (G. A.); VIVIER (V.); WINTER (M.) |
AF : | Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3/00 664 Warszawa/Pologne (1 aut., 2 aut., 3 aut.); INAC/SPrAM, UMR 5819 CEA-CNRS-University J. Fourier-Grenoble 1, Laboratoire d'Electronique Moléculaire Organique et Hybride, 17 Rue des Martyrs/38054 Grenoble/France (4 aut.); CNRS/Toulouse/France (1 aut.); Monash University/Clayton, Vic./Australie (2 aut.); University of Houston/Houston, TX/Etats-Unis (3 aut.); LEPMI/Grenoble/France (4 aut.); University of Palermo/Italie (5 aut.); Lund University/Suède (6 aut.); Eotvos Lorand University/Budapest/Hongrie (7 aut.); CNRS/Nancy/France (8 aut.); Wildau University/Allemagne (9 aut.); Polish Academy of Sciences/Warsaw/Pologne (10 aut.); Université de Strasbourg/France (11 aut.); Nanyang Technological University/Singapour (12 aut.); Moscow State University/Russie (13 aut.); Université Pierre et Marie Curie/Paris/France (14 aut.); University of Münster/Allemagne (15 aut.) |
DT : | Publication en série; Congrès; Niveau analytique |
SO : | Electrochimica acta; ISSN 0013-4686; Coden ELCAAV; Royaume-Uni; Da. 2011; Vol. 56; No. 28; Pp. 10464-10472; Bibl. 33 ref. |
LA : | Anglais |
EA : | Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-te rthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N, N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-p henylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1 ,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs. |
CC : | 001D09D04D |
FD : | Copolymère alterné; Polymère électroactif; Imide copolymère; Semiconducteur; Synthèse chimique; Spectroélectrochimie; Thiophène dérivé copolymère; Spectrométrie UV visible; Propriété électrochimique; Voltammétrie cyclique; Semiconducteur organique; Polymère conducteur; Naphtalène-1,4,5,8-tétracarboximide dérivé; Benzo[lmn][3,8]phénanthroline-1,3,6,8-tétraone dérivé |
ED : | Alternating copolymer; Electroactive polymer; Imide copolymer; Semiconductor materials; Chemical synthesis; Spectroelectrochemistry; Thiophene derivative copolymer; Ultraviolet visible spectrometry; Electrochemical properties; Cyclic voltammetry; Organic semiconductors; Conducting polymers |
SD : | Copolímero alternado; Polímero electroactivo; Imida copolímero; Semiconductor(material); Síntesis química; Espectroelectroquímica; Tiofeno derivado copolímero; Espectrometría UV visible; Propiedad electroquímica; Voltametría cíclica |
LO : | INIST-1516.354000505919820210 |
ID : | 12-0325093 |
Links to Exploration step
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<term>Spectroélectrochimie</term>
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<term>Spectrométrie UV visible</term>
<term>Propriété électrochimique</term>
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<term>Naphtalène-1,4,5,8-tétracarboximide dérivé</term>
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<front><div type="abstract" xml:lang="en">Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-terthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.</div>
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<fA18 i1="01" i2="1"><s1>International Society of Electrochemistry (ISE)</s1>
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<s1>© 2012 INIST-CNRS. All rights reserved.</s1>
</fA44>
<fA45><s0>33 ref.</s0>
</fA45>
<fA47 i1="01" i2="1"><s0>12-0325093</s0>
</fA47>
<fA60><s1>P</s1>
<s2>C</s2>
</fA60>
<fA61><s0>A</s0>
</fA61>
<fA64 i1="01" i2="1"><s0>Electrochimica acta</s0>
</fA64>
<fA66 i1="01"><s0>GBR</s0>
</fA66>
<fC01 i1="01" l="ENG"><s0>Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-terthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.</s0>
</fC01>
<fC02 i1="01" i2="X"><s0>001D09D04D</s0>
</fC02>
<fC03 i1="01" i2="X" l="FRE"><s0>Copolymère alterné</s0>
<s2>NK</s2>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="ENG"><s0>Alternating copolymer</s0>
<s2>NK</s2>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA"><s0>Copolímero alternado</s0>
<s2>NK</s2>
<s5>01</s5>
</fC03>
<fC03 i1="02" i2="X" l="FRE"><s0>Polymère électroactif</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="ENG"><s0>Electroactive polymer</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Polímero electroactivo</s0>
<s5>02</s5>
</fC03>
<fC03 i1="03" i2="X" l="FRE"><s0>Imide copolymère</s0>
<s2>NK</s2>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Imide copolymer</s0>
<s2>NK</s2>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Imida copolímero</s0>
<s2>NK</s2>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>Semiconducteur</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Semiconductor materials</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Semiconductor(material)</s0>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Synthèse chimique</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG"><s0>Chemical synthesis</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA"><s0>Síntesis química</s0>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Spectroélectrochimie</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>Spectroelectrochemistry</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>Espectroelectroquímica</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Thiophène dérivé copolymère</s0>
<s2>NK</s2>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Thiophene derivative copolymer</s0>
<s2>NK</s2>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Tiofeno derivado copolímero</s0>
<s2>NK</s2>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Spectrométrie UV visible</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Ultraviolet visible spectrometry</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Espectrometría UV visible</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Propriété électrochimique</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Electrochemical properties</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Propiedad electroquímica</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Voltammétrie cyclique</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Cyclic voltammetry</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Voltametría cíclica</s0>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="3" l="FRE"><s0>Semiconducteur organique</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="3" l="ENG"><s0>Organic semiconductors</s0>
<s5>11</s5>
</fC03>
<fC03 i1="12" i2="3" l="FRE"><s0>Polymère conducteur</s0>
<s5>32</s5>
</fC03>
<fC03 i1="12" i2="3" l="ENG"><s0>Conducting polymers</s0>
<s5>32</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Naphtalène-1,4,5,8-tétracarboximide dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>76</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Benzo[lmn][3,8]phénanthroline-1,3,6,8-tétraone dérivé</s0>
<s4>INC</s4>
<s5>91</s5>
</fC03>
<fN21><s1>247</s1>
</fN21>
</pA>
<pR><fA30 i1="01" i2="1" l="ENG"><s1>International Society of Electrochemistry (ISE) Meeting</s1>
<s2>61</s2>
<s3>Nice FRA</s3>
<s4>2010-09-26</s4>
</fA30>
</pR>
</standard>
<server><NO>PASCAL 12-0325093 INIST</NO>
<ET>Alternating copolymers of oligoarylenes and naphthalene bisimides as low band gap semiconductors: Synthesis, electrochemical and spectroelectrochemical behavior</ET>
<AU>GAWRYS (Pawel); ZOLTOWSKA (Anna); ZAGORSKA (Malgorzata); PRON (Adam); BERGEL (A.); BOND (A. M.); BRANKOVIC (S.); BULTEL (Y.); DI QUARTO (F.); GORTON (L.); INZELT (G.); LAPICQUE (F.); LISDAT (F.); OPALLO (M.); SAVINOVA (E. R.); TOH (C.S.); TSIRLINA (G. A.); VIVIER (V.); WINTER (M.)</AU>
<AF>Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3/00 664 Warszawa/Pologne (1 aut., 2 aut., 3 aut.); INAC/SPrAM, UMR 5819 CEA-CNRS-University J. Fourier-Grenoble 1, Laboratoire d'Electronique Moléculaire Organique et Hybride, 17 Rue des Martyrs/38054 Grenoble/France (4 aut.); CNRS/Toulouse/France (1 aut.); Monash University/Clayton, Vic./Australie (2 aut.); University of Houston/Houston, TX/Etats-Unis (3 aut.); LEPMI/Grenoble/France (4 aut.); University of Palermo/Italie (5 aut.); Lund University/Suède (6 aut.); Eotvos Lorand University/Budapest/Hongrie (7 aut.); CNRS/Nancy/France (8 aut.); Wildau University/Allemagne (9 aut.); Polish Academy of Sciences/Warsaw/Pologne (10 aut.); Université de Strasbourg/France (11 aut.); Nanyang Technological University/Singapour (12 aut.); Moscow State University/Russie (13 aut.); Université Pierre et Marie Curie/Paris/France (14 aut.); University of Münster/Allemagne (15 aut.)</AF>
<DT>Publication en série; Congrès; Niveau analytique</DT>
<SO>Electrochimica acta; ISSN 0013-4686; Coden ELCAAV; Royaume-Uni; Da. 2011; Vol. 56; No. 28; Pp. 10464-10472; Bibl. 33 ref.</SO>
<LA>Anglais</LA>
<EA>Three novel electroactive copolymers, consisting of alternating naphthalene bisimide and oligoarylene segments have been synthesized and studied by cyclic voltammetry and UV-vis-NIR spectroelectrochemistry. These studies show that the conjugation between both copolymer segments is very weak and the reduction of the bisimide part is essentially uninfluenced by the oligoarylene segment. The oxidation of the oligoarylene segment strongly depends on its length but is not affected by the presence of the bisimide part. The HOMO levels, determined electrochemically are systematically below -5.0 eV with respect to the vacuum level, changing from -5.45 eV for poly[1,4-phenylene-(4,3'(4'),3"-trioctyl-2,2',5',2"-te rthiophene-5,5"-diyl)-1,4-phenylene-1,4,5,8-naphthalenediimide-N, N'-diyl] (6) to -5.50 eV in poly[1,4-phenylene-(4,4'-dioctyl-2,2'-bithiophene-5,5'-diyl)-1,4-p henylene-1,4,5,8-naphthalenediimide-N,N'-diyl] (5) and -5.84eV for poly[1,4-phenylene-(3,4-dioctylthiophene-2,5-diyl)-1,4-phenylene-1 ,4,5,8-naphthalenediimide-N,N'-diyl] (4). The LUMO levels in all three cases are close to -4.0 eV. The obtained results clearly indicate that 5 and 6 are good candidates for the fabrication of ambipolar transistors operating in air whereas 4 can be considered as an active component of n-channels FETs.</EA>
<CC>001D09D04D</CC>
<FD>Copolymère alterné; Polymère électroactif; Imide copolymère; Semiconducteur; Synthèse chimique; Spectroélectrochimie; Thiophène dérivé copolymère; Spectrométrie UV visible; Propriété électrochimique; Voltammétrie cyclique; Semiconducteur organique; Polymère conducteur; Naphtalène-1,4,5,8-tétracarboximide dérivé; Benzo[lmn][3,8]phénanthroline-1,3,6,8-tétraone dérivé</FD>
<ED>Alternating copolymer; Electroactive polymer; Imide copolymer; Semiconductor materials; Chemical synthesis; Spectroelectrochemistry; Thiophene derivative copolymer; Ultraviolet visible spectrometry; Electrochemical properties; Cyclic voltammetry; Organic semiconductors; Conducting polymers</ED>
<SD>Copolímero alternado; Polímero electroactivo; Imida copolímero; Semiconductor(material); Síntesis química; Espectroelectroquímica; Tiofeno derivado copolímero; Espectrometría UV visible; Propiedad electroquímica; Voltametría cíclica</SD>
<LO>INIST-1516.354000505919820210</LO>
<ID>12-0325093</ID>
</server>
</inist>
</record>
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